The use of Privately Contracted Armed Security Personnel (PCASP) on ships transiting High Risk Areas (HRA) is a topic bounded in controversy. During 2010 and 2011 the issue was debated in depth by maritime stakeholders due to the dramatic increase of ships attacked or laid hostage by pirates in the Gulf of Aden. In response, the International Maritime Organisation during 2011 provided guidance in the form of circulars which outlined the key points that a ship-owner should consider before employing PCASP. The first part of this article explores the background that led to the concept of PCASP first being debated at the International level. The following sections continue by examining and detailing the complexities of the different legal systems that may impact on a ship owner should they choose to employ PCASP. Finally the paper concludes with the pressing International concerns and possible future consequence of PCASP on ships transiting HRAs.